Most Convoluted Timelines

For the first two films of the Terminator franchise, things make enough sense that you can more or less go along with it. It's a little strange that John Connor sent his own father back in time to impregnate his mother, but whatever. No big deal.

Things get more complicated with Terminator: Rise of the Machines where we find that the Judgement Day-preventing actions of Terminator 2 served only to postpone Judgement Day a little. Apparently fate is a stronger force than time travel, though its timetable can be nudged a bit.

By the time we get to Terminator Salvation, things are insane. John Connor is judging the future based on everything his mother taught him, but what does he do if the past he helped create affects the future he's supposed to expect?

Despite numerous trips into the past, the future, and alternate presents (and alternate pasts and alternate futures), the Star Trek timeline usually managed to get wiped clean and put back where it belonged at the end of the day.

That all changed with J.J. Abrams's take on the series. This remake? reboot? prequel? sequel? ...whatever it was, it featured Leonard Nimoy's Spock from the classic timeline time-traveling back into the Zachary Quinto Spock's present where the destruction of Vulcan creates an entire new Star Trek timeline that also fits with the continuity of the old timeline. So now there are two canon Spocks, but they each have different histories. Or the same histories but at different times. Or something like that.

You wouldn't think something like the Fast & Furious franchise would have a convoluted timeline, but it does thanks to Tokyo Drift, the third and possibly least appreciated film in the series.

This is the film that introduces the super-cool Japanese character Han. And (spoilers!) this is also the film that kills the super-cool Japanese character Han. Therefore, the next two entries in the series, both of which feature Han alive and well, are sequels to the first Fast & Furious films but prequels to Tokyo Drift. As long as they keep making new Fast & Furious films that feature Han, this timeline will continue to grow more and more convoluted.

The original Planet of the Apes series was well steeped in time travel shenanigans, but it all pretty much worked out. At the end of the fifth film, the only complication was choosing whether the whole thing was one big loop or that the future had been changed for the better. Not too bad. The recent Rise of the Planet of the Apes skipped time line complication as well since the movie was clearly not trying to be in continuity with the original series.

Tim Burton's Planet of the Apes film was also separate from the original's continuity, but it has a tangled timeline just within itself thanks to its shocking twist ending in which bad chimpanzee General Thade somehow infiltrates Earth's timeline and changes everything into Ape-Ville long before Mark Wahlberg arrives back home. This alternate version of Earth apparently had its own ape Abraham Lincoln and everything (of course it was Thade, somehow). The logistics of this new timeline are simply too silly to contemplate without giving oneself a headache. For instance: if Earth had been run by apes since the Civil War, wouldn't Mark Wahlberg cease to exist?